Read Hal Roth: Chasing the Longest Rainbow & Two Against the Horn
If you read nothing else, get all Hal Roth's books. Especially AFter 50000 Miles and Two on a Big Ocean. Not only good reading but tons of technical and sailing advice.
There are many others, but I would not attempt the horn unless you have years of experience and unless you have something to prove also have a crew. Most of the west coast of South Amereica is many nights at sea.
What's wrong with the canel? Many cruisers line handle for each other so eventually all get through. It's a little pricey but well worth it in the long run.
Do some Catalina Island and back trips ... get her feet wet on day trips. Then maybe just head out 200 miles or so for an overnighter, turn around and sail back.

The reason we want to go all the way around rather than through the canal is we want to get off the well-trodden path and see places that not many tourists / travelers get to see.

My girlfriend is not adverse to bad weather, etc., it's just that she doesn't want to be 25+ days at sea for her first extended cruise. She also would like us to eventually (when she's got some miles under her belt) to sail to Europe.

One rather obvious solution to your problem is to cruise to Baja and the west coast of Mexico. This can be done with only short (one or two day) jumps, provide you with lots of useful experience (which you seem to lack), and give you numerous bail-out opportunities should your enthusiasm wane. If all goes well, jumping off to the Marquesas from that area is a standard scheme (we've done that one twice).

If getting to unusual places is your goal, some practice in going to more usual spots would be a good game plan, for there is a good reason that such places are seldom visited: either they are not desirable cruising destinations, or they are very hard to get to.

I don't lack the experience (35 years racing and sailing including several CA to Mexico races and a year cruising Baja, Hawaii and the PNW on an old wooden schooner).

What I'm trying to find is a happy medium that will provide my girlfriend with a little bit more sense of security while she gets her sea legs, and will still satisfy my desire to get off the beaten path.

I've heard the Chilean Archipelago mentioned in a few sail blogs and I thought this might satisfy the both of us.

I'll all for jumping off to the South Pacific, but my want my girlfriend to feel comfortable (and at this point, feeling comfortable is being able to see land on the horizon).

That is why I'm looking for information from people who have cruised that area before.

We have friends travelling on a gaff schooner that made that trip over the last year and half (we joined them for the leg down NA west coast). They made their way to Galapagos then to Easter island as the counter current is a real bugger, then on to Valdiva where they really enjoyed the Chilean coast. then around the horn and on to S/A.

There is an infrequent contributor to CF, chouli, who is doing that journey now. I suggest sending him a PM, outlining your experience, your gf's lack of it, and ask your question of him, in addition to this thread. My guess is that you'll hear that the plan will be difficult to accomplish mostly due to the vagaries of checking in and out (you're expected to leave the country immediately and your entry port may be over a day's sail away).

At the same time, I'd have a chat with the GF. Pay really close attention to her body language to determine if she is sincere about wanting to push her limits, as her words are likely to be aimed at reassuring you. What you're looking for is congruency between words and body language. Some people never get over that fear of being out of sight of land. And, from what I read here on CF, women who are happy to go to sea and just see what happens, on a 30 ft. boat are scarce as hen's teeth. Your GF may or may not be one of these rare birds.

Of course, if she's inexperienced, she will have a lot to learn in order to feel safe, and she might benefit from doing some sail training. If she is interested to do that, my recommendation would be that she do it in a class for women, where such "irrational" fears as being out of sight of land can be addressed in a more supportive environment. Bear in mind, that in the absence of a lot of sailing experience, such fears are healthy, and self-protective: most sane people are wary of the unknown. A different point of view comes from acknowledging that there are dangers, and learning how to address them. The dangers on the water are different from the land dangers, and a good case can be made that there are less on the water.

It's not only learning to become a sailor that's important, her goal will need to be to be able to do all the sailing stuff you can, 'cause I'm really sure you guys will be watch on watch for a few days at a time.

Cruising isn't just about sailing, and mai tais in the sunset; it is also about maintaining boat systems. If you mislead her about what's involved in doing your projected trip, glossing it over, she is unlikely to trust you again.

I'll agree with Ann on this..On a delivery I did to Oz I had a former GF crew for me.. we'd been liveaboard's for 4yrs down W. Europe and the Med.. she'd experienced a serious SE gale in the Biscay (a bad direction against the current).. several gales in the Med and a cyclone in the Balearics..However by the time we reached American Samoa from Panama she'd had enough and flew home to the UK.. its not the physical side so much as mental strength... the 24/7 rolling and day after day of nothing but sea.. breakdowns, water shortage and praying for squalls to top up some 5 litre jugs to keep you going.. it gets seriously wearing on crew.. they don't have the same investment or drive that the skipper has.. and the question becomes.. WTF am I hereIts not all G & T's on the fore deck.. that comes after the crossings/passages.. in between desalinating and fixing the boat.. one 36ftr that year took 57 days Panama to the Marquesas..Go through the Canal.. do the Islands and the following year head for the Med.. then do the S. Pacific..

What I'm trying to find is a happy medium that will provide my girlfriend with a little bit more sense of security while she gets her sea legs, and will still satisfy my desire to get off the beaten path.

Connie and I both think the trip down is way worse then the sail around the cape!! Theres lots of great places to anchor, safe and great to lay out when the wind is to bad ! If ya are set up to be comfortable at anchor for at least a week at a time maybe, it can be a fun crossing! The trip to the cape is way windy and short of really good places to stop !! Just our 2 cents! But don't think I would do it again LOL not at my age now !

Head south thru Mexico and Western Central America. You can do that entire trip with only a couple over night legs. A pleasant trip that will expose GF to beautiful and gentle sailing over a period of many months.

When you get to Panama your GF will have either:

1 - decided she loves sailing and multi-day at sea legs
2 - she does not want to do any overnight legs but wants to keep sailing
3 - she hates sailing

If 1 - then keep going south
If 2 - head east thru the canal
If 3 - find another GF or sell the boat

But - you won't know the answer until you take her for some extended sailing trips outside the US in a real cruising mode.

I'd also advocate for women's sail training. I loved it. Here's what it taught me:

I never trust a man speaks for his gf on a forum like this; she's the one who should be on here asking the questions. Sorry. But I don't want you guys to get out in a nasty situation because she is trying to make you happy. I wouldn't even dream of what you're contemplating without years of experience and a badass boat. Taking a novice, uncertain person would make me very frightened. I wouldn't trust a captain who suggested it, no matter his own sailing experience. Each person on a trip must be able to confidently make the trip on their own. She doesn't sound ready for that. Don't mean to bust your chops though, just worried for your safety.

Great she is interested in the idea. Start *on the beaten path*, then decide to get off it. I mean, just cruising at all is off the beaten path, isn't it?